5-Nitrofurfural → HCID 86623883, compound

HRID 1696660Notes

Reaction equation

HRID 1696660 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:14])[C:11]([Cl:13])=[CH:12][C:6]=2[N:5]=1.[N+]([C:18]1[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1)([O-])=O>O1CCCC1>[Cl:13][C:11]1[C:10]([CH3:14])=[CH:9][C:7]2[NH:8][C:4]([S:3][C:18]3[O:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=3)=[N:5][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178422366HCID 178422366, compound

Product 1

HCID 86623883HCID 86623883, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Aldehyde intermediate preparation: A mixture of sodium hydride (60% dispersion in mineral oil, 0.338 g, 8.46 mmol) and 2-mercapto-5-chloro-6-methyl-1H-benzimidazole (1.05 g, 5.29 mmol) in 35 ml of tetrahydrofuran is stirred at room temperature for 2 hours. 5-nitro-2-furaldehyde (0.746 g, 5.29 mmol) in 7 ml of tetrahydrofuran is then added dropwise over a 15 minute period and the mixture is stirred for 16 hours at room temperature. The reaction mixture is then concentrated under reduced pressure and dissolved in 100 ml ethyl acetate and washed with water (2×30 ml). The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is triturated in diisopropylether and pentane and dried under vacuum to yield 854 mg of 5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde. Yield=55%. Analytical LC/MS (method B): retention time=3.64 min, m/z=272.97 (1Cl, positive ion mode).

Workup

  1. stirringthe mixture is stirred for 16 hours at room temperature
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. dissolutiondissolved in 100 ml ethyl acetate
  4. washwashed with water (2×30 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is triturated in diisopropylether
  8. dry with materialpentane and dried under vacuum

Sources & evidence

ORD record
ord-d57cd9e9ed7a460db6e76ca4f73a0bd4
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

Loading…